Pickpocket

You must be in Stealth mode to take an item from an NPC. While you can examine an NPC's inventory without incurring a Bounty, stealing something from them is criminal. Each item when selected will show a percent rate for a sucessful steal. So the the higher the percent the more chance you will have of taking the item or gold without being caught. Naturally the more valuable the item the lower the percentage for a successful steal is.

If your pickpocketing skill is well developed, your theft will not be detected. However, if you are detected by the NPC or other witnesses, you will not only be unable to take the item, but you will also be branded a criminal, and a bounty will be placed on you.

To level Pickpocketing faster, find someone with an item that either has very high value or low chance of stealing it. Then make a save and attempt to steal that item. If caught, reload save. Items with enchantments are very good. Garnets and other gems are also good targets. The thieves guild should provide you with boots that enhance your pickpocketing(15%). On one of the citizens of whiterun, you should find a neckalace of minor sneaking. This is important because you must be undetected to steal most items without getting caught.

The NPC who can train you in pickpocketing is Silda the Unseen. Silda can be found walking around in Windhelm.

Combat pickpocketing

To the master thief, no armour nor weapon can protect their victims.Hehe, yup! if you have the last two perks for pickpocketing, you can sneak up on a target and rob them of their weapons and armour, then kill them and leave their bodies disgraced and nude on the ground. This comes as a great perk for those who dont want to invest in the assassins blade perk or for those who want that extra damage without the Dark Brotherhood gloves. Also, what is more hilarious then a pack of nude Forsworn attacking you with nothing but their fists?

Tips

The "extra pockets" perk is why most people delve into pickpocketing. 100 capacity is invaluable in every way. From picking up more loot, to carrying that extra 3 sets of heavy armour you want to sell, this perk is highly recommended.